4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles

Yu P. Bandera, O. S. Kanishchev, V. M. Timoshenko, Sergii Buth, A. M. Nesterenko, Yu G. Shermolovich

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Treatment of 4-aryl(benzyl)sulfonyl-5-polyfluoroalkyl-v-triazoles with NaOCl gave the 4-aryl(benzyl)-sulfonyl-2-chloro-5-polyfluoroalkyl-v-triazole derivatives which contain a chlorine atom only on the N(2) atom of the heterocycle. The structure of 2-chloro-5-(1,1,2,2,3,3-hexafluoropropyl)-4- (p-tolyl-sulfonyl)-2H-[1,2,3]triazole has been established by X-ray structural investigation. The presence of a highly polarized N-Cl bond with a positive halogen atom causes the N-chlorotriazoles to react with KCN and KF as strong acids to form the potassium salts of the triazoles and to form 4-arylsulfonyl-2-(2-chloro-1-ethoxyethyl)-5-polyfluoroalkyl-2H-[1,2,3]triazoles with vinyl ethyl ether. It was found that chlorination of 4-arylsulfonyl-5- polyfluoroalkyl-v-triazoles in the presence of KF gives 4-chloro-5- polyfluoroalkyl-2H-[1,2,3]triazoles.

Original languageEnglish (US)
Pages (from-to)1138-1147
Number of pages10
JournalChemistry of Heterocyclic Compounds
Volume43
Issue number9
DOIs
StatePublished - Sep 2007
Externally publishedYes

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Triazoles
Atoms
Halogens
Chlorination
Chlorine
Potassium
Salts
Derivatives
X rays
Acids

Keywords

  • 1,1-dihydropolyfluoroalkyl sulfone
  • N-chlorotriazole
  • V-triazole
  • X-ay structural analysis

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Bandera, Y. P., Kanishchev, O. S., Timoshenko, V. M., Buth, S., Nesterenko, A. M., & Shermolovich, Y. G. (2007). 4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles. Chemistry of Heterocyclic Compounds, 43(9), 1138-1147. https://doi.org/10.1007/s10593-007-0175-x

4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles. / Bandera, Yu P.; Kanishchev, O. S.; Timoshenko, V. M.; Buth, Sergii; Nesterenko, A. M.; Shermolovich, Yu G.

In: Chemistry of Heterocyclic Compounds, Vol. 43, No. 9, 09.2007, p. 1138-1147.

Research output: Contribution to journalArticle

Bandera, YP, Kanishchev, OS, Timoshenko, VM, Buth, S, Nesterenko, AM & Shermolovich, YG 2007, '4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles', Chemistry of Heterocyclic Compounds, vol. 43, no. 9, pp. 1138-1147. https://doi.org/10.1007/s10593-007-0175-x
Bandera, Yu P. ; Kanishchev, O. S. ; Timoshenko, V. M. ; Buth, Sergii ; Nesterenko, A. M. ; Shermolovich, Yu G. / 4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles. In: Chemistry of Heterocyclic Compounds. 2007 ; Vol. 43, No. 9. pp. 1138-1147.
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abstract = "Treatment of 4-aryl(benzyl)sulfonyl-5-polyfluoroalkyl-v-triazoles with NaOCl gave the 4-aryl(benzyl)-sulfonyl-2-chloro-5-polyfluoroalkyl-v-triazole derivatives which contain a chlorine atom only on the N(2) atom of the heterocycle. The structure of 2-chloro-5-(1,1,2,2,3,3-hexafluoropropyl)-4- (p-tolyl-sulfonyl)-2H-[1,2,3]triazole has been established by X-ray structural investigation. The presence of a highly polarized N-Cl bond with a positive halogen atom causes the N-chlorotriazoles to react with KCN and KF as strong acids to form the potassium salts of the triazoles and to form 4-arylsulfonyl-2-(2-chloro-1-ethoxyethyl)-5-polyfluoroalkyl-2H-[1,2,3]triazoles with vinyl ethyl ether. It was found that chlorination of 4-arylsulfonyl-5- polyfluoroalkyl-v-triazoles in the presence of KF gives 4-chloro-5- polyfluoroalkyl-2H-[1,2,3]triazoles.",
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AU - Kanishchev, O. S.

AU - Timoshenko, V. M.

AU - Buth, Sergii

AU - Nesterenko, A. M.

AU - Shermolovich, Yu G.

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AB - Treatment of 4-aryl(benzyl)sulfonyl-5-polyfluoroalkyl-v-triazoles with NaOCl gave the 4-aryl(benzyl)-sulfonyl-2-chloro-5-polyfluoroalkyl-v-triazole derivatives which contain a chlorine atom only on the N(2) atom of the heterocycle. The structure of 2-chloro-5-(1,1,2,2,3,3-hexafluoropropyl)-4- (p-tolyl-sulfonyl)-2H-[1,2,3]triazole has been established by X-ray structural investigation. The presence of a highly polarized N-Cl bond with a positive halogen atom causes the N-chlorotriazoles to react with KCN and KF as strong acids to form the potassium salts of the triazoles and to form 4-arylsulfonyl-2-(2-chloro-1-ethoxyethyl)-5-polyfluoroalkyl-2H-[1,2,3]triazoles with vinyl ethyl ether. It was found that chlorination of 4-arylsulfonyl-5- polyfluoroalkyl-v-triazoles in the presence of KF gives 4-chloro-5- polyfluoroalkyl-2H-[1,2,3]triazoles.

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KW - X-ay structural analysis

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